De Novo Structure-Based Design of Bis-amidoxime Uranophiles

Vukovic, Sinisa; Hay, Benjamin P.

doi:10.1021/ic401089u

Cited by 50 publications

(61 citation statements)

References 59 publications

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“…From a chemistry perspective, general principles that are used by nature for realizing these additional mutations to exert control over the binding affinity, include enforcing a correct geometry, exerting charge stabilization, and providing proper hydrogen bond interactions to the distal sites off of the metal centers 21 , 22 . In this context, it is anticipated that both the stability and selectivity of uranyl chelates will be enhanced when these concepts are included, in addition to coordinative binding with the metal center.…”

Section: Introductionmentioning

confidence: 99%

Bio-inspired nano-traps for uranium extraction from seawater and recovery from nuclear waste

et al. 2018

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Nature can efficiently recognize specific ions by exerting second-sphere interactions onto well-folded protein scaffolds. However, a considerable challenge remains to artificially manipulate such affinity, while being cost-effective in managing immense amounts of water samples. Here, we propose an effective approach to regulate uranyl capture performance by creating bio-inspired nano-traps, illustrated by constructing chelating moieties into porous frameworks, where the binding motif’s coordinative interaction towards uranyl is enhanced by introducing an assistant group, reminiscent of biological systems. Representatively, the porous framework bearing 2-aminobenzamidoxime is exceptional in sequestering high uranium concentrations with sufficient capacities (530 mg g−1) and trace quantities, including uranium in real seawater (4.36 mg g−1, triple the benchmark). Using a combination of spectroscopic, crystallographic, and theory calculation studies, it is revealed that the amino substituent assists in lowering the charge on uranyl in the complex and serves as a hydrogen bond acceptor, boosting the overall uranyl affinity of amidoxime.

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Section: Introductionmentioning

confidence: 99%

Bio-inspired nano-traps for uranium extraction from seawater and recovery from nuclear waste

et al. 2018

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“…Open chain amidoxime is claimed to bind UO 2 2+ in η 2 coordination through the oxygen and nitrogen of the oxime (Scheme 1). On the other hand, the cyclic imide dioxime forms a tridentate coordination for UO 2 2+ with a higher binding constant [28].…”

Section: Introductionmentioning

confidence: 99%

Novel poly(imide dioxime) sorbents: Development and testing for enhanced extraction of uranium from natural seawater

Das

Brown

Mayes

et al. 2016

Chemical Engineering Journal

145

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A new series of amidoxime-based polymer adsorbents were synthesized at the Oak Ridge National Laboratory (ORNL) by electron beam induced grafting of acrylonitrile and itaconic acid onto polyethylene fiber. Hydroxylamine derivatives of poly(acrylonitrile) (PAN) moiety are demonstrated to possess two kinds of functional groups: open-chain amidoxime and cyclic imide dioxime. The open-chain amidoxime is shown to convert to imide dioxime on heat treatment in the presence of an aprotic solvent, like dimethylsulfoxide (DMSO). The formation of amidoxime and imide dioxime was confirmed by 13 C CP-MAS spectra. The adsorbents were evaluated for uranium adsorption efficiency at ORNL with simulated seawater spiked with 8 ppm uranium and 5 gallon seawater in a batch reactor, and in flow-through columns with natural seawater at the Marine Science Laboratory (MSL) of Pacific Northwest National Laboratory (PNNL) at Sequim Bay, WA. The DMSO-heat-treated sorbents adsorbed uranium as high as 4.48 g-U/Kg-ads. from seawater. Experimental evidence is presented that the poly(imide dioxime) is primarily responsible for enhanced uranium adsorption capacity from natural seawater. The conjugated system in the imide dioxime ligand possesses increased electron donation ability, which is believed to significantly enhance the uranyl coordination in seawater.

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“…PCMODEL has been used in a number of studies ( e.g ., refs. 36-40). PCMODEL-computed bond distances and angles, as well as the global minimal energy conformation, of organic molecules agree approximately with those determined by X-ray diffraction in the crystal form (36, 37).…”

Section: Methodsmentioning

confidence: 99%

A New VGLUT-Specific Potent Inhibitor: Pharmacophore of Brilliant Yellow

2013

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The increased concentration of glutamate in synaptic vesicles, mediated by the vesicular glutamate transporter (VGLUT), is an initial vital step in glutamate synaptic transmission. Evidence indicates that aberrant overexpression of VGLUT is involved in certain pathophysiologies of the central nervous system. VGLUT is subject to inhibition by various types of agents. The most potent VGLUT-specific inhibitor currently known is Trypan Blue, which is highly charged, hence membrane-impermeable. We have sought a potent, VGLUT-specific agent amenable to easy modification to a membrane-permeable analog. We provide evidence that Brilliant Yellow exhibits potent, VGLUT-specific inhibition, with a Ki value of 12 nM. Based upon structure-activity relationship studies and molecular modeling, we have defined the potent inhibitory pharmacophore of VGLUT Brilliant Yellow. This study provides new insight into development of a membrane-permeable agent to lead to specific blockade, with high potency, of accumulation of glutamate into synaptic vesicles in neurons.

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De Novo Structure-Based Design of Bis-amidoxime Uranophiles

Cited by 50 publications

References 59 publications

Bio-inspired nano-traps for uranium extraction from seawater and recovery from nuclear waste

Bio-inspired nano-traps for uranium extraction from seawater and recovery from nuclear waste

Novel poly(imide dioxime) sorbents: Development and testing for enhanced extraction of uranium from natural seawater

A New VGLUT-Specific Potent Inhibitor: Pharmacophore of Brilliant Yellow

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